Triethylamine → 2-Methoxymethyl-4-[4-(pyrrolidine-1-sulfonyl)-piperazin-1-yl]-pyrimidine

HRID 586176

Reaction equation

HRID 586176 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[N:9]=[C:8]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:7]=[CH:6][N:5]=1.C(N(CC)CC)C.[N:23]1([S:28](Cl)(=[O:30])=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24]1>O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][CH2:3][C:4]1[N:9]=[C:8]([N:10]2[CH2:15][CH2:14][N:13]([S:28]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)(=[O:30])=[O:29])[CH2:12][CH2:11]2)[CH:7]=[CH:6][N:5]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 64839021-Pyrrolidinesulfonyl chlorideHCID 109547722-Methoxymethyl-4-piperazin-1-yl-pyrimidine

Product 1

HCID 223287382-Methoxymethyl-4-[4-(pyrrolidine-1-sulfonyl)-piperazin-1-yl]-pyrimidine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-methoxymethyl-4-piperazin-1-yl-pyrimidine (prepared according to the method of Preparation One, 2.08 g, 10 mmol) and triethylamine (1.01 g, 10 mmol) in tetrahydrofuran (20 mL) was added N-pyrrolidinesulfonyl chloride (1.69 g, 10 mmol) at 0° C. and stirred for 3 h at ambient temperature. The mixture was diluted with ethyl acetate and washed twice with water. The organic layer was separated, dried over magnesium sulfate, filtered, and the filtrate was concentrated to an oil which was purified by flash chromatography (95:5 dichloromethane:methanol) to give the title compound of Example 121, Step A as a clear oil, 3.24 g (93%). 1H NMR (CDCl3, 300 MHz) δ 1.81-1.85 (m, 4H), 3.12-3.18 (m, 8H), 3.59 (s, 3H), 3.81 (m, 4H), 4.43 (s, 2H), 6.71 (d, 1H), 8.18 (d, 1H); MS (TS) 342 (MH+).

Workup

  1. washwashed twice with water
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated to an oil which
  6. customwas purified by flash chromatography (95:5 dichloromethane:methanol)

Sources & evidence

ORD record
ord-09fb55001e3945a1915a9bced150657f
Source dataset
uspto-grants-2005_08
Patent number
US06936600B2

Linked notes

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